Trifluoroacetic acid → 5-Benzyloxy-2-[2-(1,2,3,4-tetrahydro-isoquinolin-7-yl)-ethyl]-2H-pyridazin-3-one

HRID 564187Notes

Reaction equation

HRID 564187 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH2:18][CH2:19][N:20]3[C:25](=[O:26])[CH:24]=[C:23]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:22]=[N:21]3)=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:28]([O:27][C:23]1[CH:22]=[N:21][N:20]([CH2:19][CH2:18][C:12]2[CH:11]=[C:10]3[C:15]([CH2:16][CH2:17][NH:8][CH2:9]3)=[CH:14][CH:13]=2)[C:25](=[O:26])[CH:24]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 670069227-[2-(4-Benzyloxy-6-oxo-6H-pyridazin-1-yl)-ethyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic Acid Tert-Butyl Ester

Product 1

HCID 580427515-Benzyloxy-2-[2-(1,2,3,4-tetrahydro-isoquinolin-7-yl)-ethyl]-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 30 mg (0.06 mmol) 7-[2-(4-benzyloxy-6-oxo-6H-pyridazin-1-yl)-ethyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (example 25.1a) in 2.0 mL DCM is added 50 μL trifluoroacetic acid at RT. The solvent is evaporated and the residue is purified via reverse HPLC chromatography (Waters SunFire, C18; water (0.1% formic acid)/acetonitrile (0.1% formic acid) 95:5 to 10:90).

Workup

  1. customThe solvent is evaporated
  2. customthe residue is purified via reverse HPLC chromatography (Waters SunFire, C18; water (0.1% formic acid)/acetonitrile (0.1% formic acid) 95:5 to 10:90)

Sources & evidence

ORD record
ord-1e4d054e569e4d5e92469cbbfb1f8953
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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